An imide ether compound is a useful compound as a raw material of ortho-ester compound or the like, which is widely used in medical drug, agricultural chemical and industrial fields. By subjecting an alphatic nitrile or an aromatic nitrile, alcohol and hydrogen chloride, as raw materials, to a reaction, an imide ether hydrochloride, which is solid at normal temperature, can be formed.
Several methods for producing an imide ether compound are also known, for example, a method for generating an acetimide ether hydrochloride is disclosed (JP-B-61-28663), wherein the first step is carried out to react an alcohol in an amount of 0.3 to 0.6 mole and hydrogen chloride in an amount of 1.0 to 1.5 moles, relative to 1 mole of acetonitrile, and then by the addition of 0.4 to 0.8 mole of the alcohol into the resultant reaction liquid, the second step is carried out to continue an acetimide etherification reaction in the co-presence of a dispersing medium. Because an objective substance is deposited as crystal with progress of the acetimide etherification, and thickening of slurry-like reaction liquid makes it difficult to introduce theoretical amount of hydrogen chloride gas, the first step is carried out while suppressing deposition of the crystal by using 0.3 to 0.6 mole of the alcohol in advance, and then acetimide etherification reaction is completed by the further addition of the alcohol to the resultant reaction liquid in carrying out the second step. It should be noted that the dispersing medium is added to secure fluidity in the second step.
In addition, a method for generating an alkyl imide ether hydrochloride by the addition of a nitrile compound into an alcohol solution dissolved with hydrogen chloride is also disclosed (JP-A-2000-191618). The present invention was developed in view of a problem that the method for blowing hydrochloric gas into an alcohol solution of an aliphatic nitrile generates simultaneously the heat of dissolution of hydrogen chloride into a solvent and the heat of reaction, and heat generation amount is too much, and thus makes control of reaction temperature difficult. Namely, by dissolving hydrogen chloride into the alcohol in advance, heat of dissolution of hydrogen chloride during the reaction is suppressed, thereby reaction temperature is controlled and workability is improved.
In the meantime, in the production step of a compound, various reaction apparatuses are used. For example, in a method for producing an alkaline metal salt of glycine in which glycinonitrile and alkaline metal hydroxide are subjected to a reaction in the presence of water solvent, the reaction is carried out using a stirring tank flow reactor pressurized so that partial pressure of ammonia becomes at least equal to or higher than 0.2 MPa, and the reaction of the resultant reaction solution is completed in a liquid-sealing type tubular flow reactor (JP-A-2003-192650). By introduction ammonia into the stirring tank flow reactor while increasing a pressure so that partial pressure of ammonia becomes at least equal to or higher than 0.2 MPa, the reaction can be completed in a liquid sealing state, without vaporization of by-produced ammonia gas, and coloring of the reaction solution can be suppressed by setting arbitrarily ammonia concentration in a system.
In addition, a method for producing a concoction containing skin cosmetic ingredients, by the procedure step for inducing the concoction or the like, containing skin cosmetic ingredients, by an apparatus having a microstructure unit such as a micro-mixer or the like, is known (JP-A-2003-321325). It is an object of this invention to attain homogenization by using a micro-mixer or the like, in view of a problem that degree of homogenization affects quality or the like of final products in an emulsion concoction, and non-uniformity of emulsion particles has conventionally not fulfilled sufficient effect.
In addition, a method for producing a Friedel-Crafts type monoalkylation reaction substance in high selectivity, by subjecting an aromatic compound and an alkylating agent to a reaction in a micro-reactor, is also known (JP-A-2004-99443). In this reaction, mixing of 2 miscible liquids in micro-mixer results in rough spreading of relatively large fluid assembly throughout the reactor, turbulent diffusion by vortex, mixing in a gradually finer range, and then rapid progressing of a reaction in micro-space, by which high selectivity is provided.
It should be noted that “a micro-reactor” is a general name of a very small reactor having a micro fluid passage of several to several hundreds μm, having such features as:
(1) high heating and cooling rate
(2) laminar flow
(3) large surface area per unit volume
(4) rapid progress of a reaction due to short diffusion length of a substance